Playdate
by PhoenixRisingOnTheMoon
Summary: In which Regina is Henry's kindergarten teacher, and Emma works a little too hard at impressing her. Swan-Mills family fluff.


Disclaimer: I don't own anything.

A/N: based on a tweet from XplodingUnicorn about his daughter. this was written shortly after completing my last day at my job from hell, so half of this was an attempt at actually writing something decent and the other half was just me letting out all of my salt and sarcasm that was pent up for the past few months, so sorry for the awkward feel. hope you enjoy!

* * *

Emma wiped her hands nervously on her pants as she stood outside the door to her son's classroom. The door was decorated with an apple tree, with each of the apples containing a child's name— Henry's was near the trunk, underneath an apple labeled "Miss Mils," the teacher that Emma was going to meet today.

She didn't really know how these parent-teacher conferences worked. Did she just walk in? What if she was meeting with another parent? While helpful on some aspects of these meetings, her Google search result didn't tell her how things specifically worked at Storybrooke Elementary.

Before she could come to a decision, the door opened and a couple stepped out— a petite brunette and a blonde man.

They both smiled upon the sight of Emma. "Hello!"

Emma gave an awkward wave. "Uh, hi."

The two moved out of her way. "Good luck," the man whispered seriously as they walked by.

Great. Emma took a deep breath and walked through the door, closing it behind her.

The classroom was full of vibrant colors, with large letters, numbers, and pictures neatly lining the walls. There were two paint easels by the large window in the back, and a couple large trunks of what Emma assumed were toys. A rug sat off to the corner with beanbag chairs and a bookcase nearby. In the adjacent corner sat a circle of chairs. There were a couple of tables with chairs in the center of the room, and as Emma's eyes moved to the left, she found the teacher sitting primly at her pristine desk.

Miss Mills' head was bent over a notepad where she was jotting something down, her dark hair curtaining her face. "You may take a seat right there, Miss Swan," she said without moving her head, pointing with her pen to the child's chair in front of her desk.

Emma did as she was told, her knees scrunching up to her chest. She spread her legs a bit in an effort to create more comfort as she waited for Miss Mills, which caused one of her legs to start bouncing up and down as the nerves started to run full force.

Finally, the woman looked up, and Emma was stunned for a brief second as her eyes connected with dark brown. _Damn she's pretty_. Emma opened her mouth but nothing came out.

"Good afternoon," she greeted as she folded her hands in front of her, glancing down at Emma's legs for less than a second before looking back up with a sly smile. "Do I make you nervous, Miss Swan?"

Emma licked her dry lips and shook her head. "No, no, it's not you, I just… I've never done one of these before."

"You have nothing to fear, Miss Swan," Miss Mills said, shuffling a couple papers on her desk and bringing one to the front, glancing at it. "Academically, your son Henry is excelling at most everything. He has a very creative mind and is always engaged in classroom discussion." She paused. "Socially, he seems to be having some trouble."

"Socially?" Emma asked.

"To be blunt," Miss Mills said, "he isn't making any friends."

Emma snorted. "We're not that far into the school year, is my son's social life really an issue?"

Miss Mills gave her a hard look. "Social development is a critical part of a child's life. Social skills are integral to obtaining and keeping careers, fostering healthy relationships and maintaining them… Studies have shown that children who do not form attachments can develop behavioral problems—"

"Is Henry acting up in class?" Emma interjected. "I've taught him his whole life to be a good kid and to not bully or—"

"No, Miss Swan," Miss Mills interrupted. "He is not acting up, _yet_. He is simply… reclusive." She paused and seemed to question whether or not to say something. "Has he… had problems forming relationships before?"

Emma shrugged. "I mean… kind of? I usually had a babysitter come to take care of him one on one rather than sending him to an expensive daycare. And we just moved to this area, so he doesn't know anyone, not that he would anyway because he's freaking _five_ — sorry— and I mean I don't even know anyone, really—" she stopped as she realized she was starting to ramble. "Sorry, I just…" She took a deep breath. "This is all my fault, isn't it? I should have paid the extra money for daycare, and I should've settled us down in the area sooner, and maybe done those 'Mommy and Me' classes or something—"

"Miss Swan." Deep brown eyes met Emma's sea green ones once more. "I am not placing the blame on you. Some children have a harder time regardless of how they are raised. I have seen children who have gone through 'Mommy and Me' classes that have been in worse positions than Henry. Besides, this is nothing permanent. That's why we have these conferences— to address the problems early so that they can be resolved as soon as possible." She gave what seemed like an attempt at a comforting smile.

Emma nodded. "Yeah, yeah, okay. Do you… have suggestions?"

Miss Mills reached into a bucket placed to the side of her desk (is that a trash can?) and pulled out a sheet of paper, sliding it over to Emma. "One suggestion I may have, although not one I would suggest as the primary option, is joining a parent group and meeting other parents, and then arranging social sessions between your children through that."

"Social sessions?" Emma asked, an amused smirk crossing her face. "You mean playdates?"

This earned her another eyebrow raise. "Yes, Miss Swan, playdates."

Emma glanced through the sheet about the PTA and saw the dates and times listed for the meetings for that entire school year. She grimaced. "I don't know if I could. I have to work the night shift down at the station once a week— I wouldn't even have the time to attend half of these." She looked up at the brunette teacher as she dropped the paper back on the desk.

"Good," Miss Mills said quickly. She closed her eyes briefly before opening them again. "What I mean to say is that the president of the group, Miss Blanchard, is… quite a handful."

"Ah," Emma said with a laugh, "one of _those_ parents?"

Miss Mills nodded, and the corners of her mouth turned upwards slightly. "Indeed." She took the paper and threw it back into the trash. "You can also sign Henry up for a sports team. We have training leagues, and I know sign ups for basketball should be starting soon."

Emma nodded. "Alright, I'll talk to him and see if he wants to try something new." There was a moment of silence between the two. "Is… is that it?"

Miss Mills nodded. "I have only been Henry's teacher for a couple of months, so there isn't necessarily going to be a lot to say. This is a good sign, Miss Swan— Henry is not disruptive, he is not a bully, and he does not cause unwanted and unneeded commotions. He is doing all of his work and is doing very well in the various subjects we've learned so far." She paused. "You should be proud."

Emma let a cheesy grin slide across her face. "All in a day's work," she joked.

All that got her was yet another eyebrow raise, though she could see amusement on Miss Mills' face.

Clearing her throat, Emma struggled up from the short stool-of-a-chair and stood awkwardly. "Well, uh… thanks for meeting with me."

"Technically _you_ were the one who met _me_ ," Miss Mills replied. "These conferences are mandated by the school."

"Semantics," Emma replied with a smile. "Oh!" she patted her pockets her phone and pulled it out. "Can I get your contact information?"

Miss Mills paused in her movements to stare at the blonde. "My what?"

"Contact information," Emma repeated. "Like, email, phone number… whatever is the best form of communication for us."

The teacher gave a short laugh. "Miss Swan, are you really asking me for my number?"

"Yeah, obviously—" Emma stopped short as she realized the implication. Her eyes widened. "Oh! No! Nononono." She gave an uncomfortable laugh. "I'm not asking you for your _number_ number, because that would be inappropriate, probably—I mean if circumstances were different—shit, sorry— I, uh… I didn't really know what to expect from this… meeting, so I did a Google search on what to do and some parent website said to get the best form of contact information for the teacher…" She took a breath laughed again. "I'm… I'm sorry, this is… way too awkward now."

Miss Mills gave a deep chuckle, but reached into a drawer. She pulled out a sticky note and jotted down something. "Here is my school email and my extension," she said as she handed Emma the note. "Completely professional," she added with a smirk.

"Thanks," Emma said, embarrassed. "So I'll, uh… see you around?"

"I should hope so," Miss Mills said, and Emma wondered if she was actually hearing her right. "The open house is next week— we'll be showcasing some of Henry's schoolwork from the past few weeks."

"Shit, yeah," Emma said. "I almost forgot about that." She stuffed her hands in her pockets. "Well, thanks for the reminder." She gave a small wave as she walked towards the door. "See you next week then."

"I look forward to it, Miss Swan," she heard Miss Mills reply as she closed the door behind her.

* * *

Emma nervously opened up her email. She had sent a message to Miss Mills last night asking about the details for the open house, because Henry conveniently forgot all of the information on it, and she may have already accidentally thrown out the paper that was given a few weeks prior.

As she predicted, an email was sitting in her inbox from Miss Mills.

 _Miss Swan,_

 _The open house begins at 6:00 on Thursday and will run till 8:00._

 _There will be activities taking place in the extracurricular activities rooms, such as the gym and the art room. You and your son would be welcome to explore the school at your leisure, though it is highly encouraged that you stop by my classroom to see what Henry has created in school thus far._

 _Sincerely,_

 _Regina Mills_

 _Regina_ , Emma thought to herself with a smile.

* * *

"This way, Mama!"

Emma smiled as she let her son drag her through the halls towards his classroom. It was the night of the open house, and Henry was overly ecstatic about showing her what he had done in school so far.

There was a light crowd in the room when the entered. Emma saw the couple from the day of the conference fawning over a drawing of a stick figure hanging on the wall, a small brunette boy resting in the father's arms.

"Alright, kid, whatcha got?" Emma asked.

Henry quickly ran towards the wall with the bookcase. He eagerly pointed up at a picture. As Emma got closer, she noticed the picture was of a collection of stick figures, each with its own unique trait. She figured the smaller one with brown hair was Henry. There was a taller one with blonde hair and… a sword? And a green stick figure with a long pink tongue that was underneath a brown bench?

"Uh… What's going on in this picture, Henry?"

"That's _you_ , Mama!" he said, as if it was the most obvious thing in the world. "You're the knight that keeps me safe!"

Emma smiled. "I'm a knight?"

"Yeah! You keep the monsters away from under my bed, and you keep the bad guys in jail," Henry stated, "and that's what knights are all about!"

"This is really sweet, Henry," Emma said. She squinted her eyes at him. "Are you sure you're not a professional artist?"

Henry giggled. "Nope!" He looked to the side and was immediately distracted by a friend of his, whom he ran over to.

Emma took the chance to look back at the picture he drew, happiness washing over her as she thought about the meaning behind it.

"Henry is completely enamored with you, Miss Swan," a familiar voice said from behind.

Emma turned to see Regina Mills standing there, looking as perfect as she had at their parent-teacher conference. She was wearing a red blouse with a black pencil skirt, and— heels? What kind of _kindergarten_ teacher wore heels?

"Is he?" Emma asked.

"Yes, quite," she replied, as she looked at the picture Henry drew. "During our sharing sessions on Wednesdays, he always tells us about your heroic feats as the sheriff." She smirked. "Even the time you braved all the odds to save your neighbor's cat from the tree."

Emma felt her face redden slightly. "Hey, that was pretty heroic. It was raining and… that tree was really hard to climb! I even slipped at one point and got a nasty gash in my side—" She pulled up the side of her shirt slightly, showing the still marred skin there to prove her point.

Regina's eyes latched onto Emma's side until Emma pulled her shirt back into its regular position. "Yes, well… you should be more careful, Miss Swan."

"I'll try my best," she replied, noticing how Regina was suddenly very interested in the drawing. "I've always wanted to be a hero," she said quietly.

"You're number one in your son's books," Regina replied with a small smile.

Emma smiled back, but before she could respond, she was pushed forward by a blunt force at the back of her knees. She stumbled, and braced herself with one of her hands on the wall— or what she thought was the wall, but was actually Regina's shoulder. The older woman's hand came to Emma's waist to help steady her. The two locked eyes for a moment.

A voice from below interrupted them. "Mama!" Emma looked down to see Henry still attached to her legs.

"Henry Swan," she admonished, "what have I told you about sneaking up on people and roughhousing?"

He pouted out his lower lip. "…Not to do it…"

"That's right, Mister," Emma said. "You gotta be careful. I almost knocked over Miss Mills."

Henry looked up at the teacher. "I is sorry!"

"I _am_ sorry," Regina corrected.

Henry shook head head in confusion. "Why are you sorry?"

Regina just laughed in response, and Emma found herself transfixed by the genuine sound.

"Mama!" Henry exclaimed again. Emma diverted her attention back to him. "Gym now!"

"The gym? What's so special about the gym?"

Henry started tugging on her hand. "You has to meet Mr. Humbert! And we gets to play games!"

"Oh yeah." Emma remembered Regina's email. "Alrighty, whatever you say, kid," Emma said. As Henry started to pull her along she glanced back at Regina. "See you around?"

Regina nodded. "I certainly hope so, considering I'm your son's teacher," she said sarcastically.

Emma grinned and was about to reply when Henry let out another complaint. She settled for a wave as they exited and headed towards the gym.

* * *

Emma heard the ping of a new message in her email. She looked and saw that the sender was— Regina Mills? What could she possibly need?

 _Miss Swan,_

 _I am writing to inquire on the status of Henry's homework from Monday night. Up until now he has always been on time with his assignments, and his lack of timeliness on this one has caused me concern—_

Emma stopped reading. Monday night? That was… Emma sighed. That was the day she had the night shift. Clearly she needed to have a talk with the new babysitter about making sure Henry got his homework done.

She skimmed through the rest of the email and started crafting her apology response.

* * *

"Hey! Use your turn signal you stupid fu—" Emma caught herself before she said anything further to corrupt her five-year-old son.

It didn't matter anyway, because her son giggled from the back seat and piped up, "You almost said a bad word!"

"No, Henry, Mommy didn't almost—"

"Yes you did—"

"No—"

"Yeessss—"

"How was school?" she interrupted, trying to change the subject as quickly as possible.

"It was _ah-maz-ing_!" Henry exclaimed in excitement as he started wriggling around in his carseat. "We learneded a song about the weekdays! Tuesday's spaghetti, so that means we should have some for supper tonight."

Emma furrowed her eyebrows as she pulled into the driveway. "Tuesday's what?"

Henry didn't seem to hear her as he continued to babble on. "And we gets to go to the zoo next week!"

Emma turned off the ignition and got out, helping Henry get out as well. As soon as his feet were on the ground he thrust his backpack into her arms.

"You can go too, Mommy!"

"Me?" she asked, ruffling his hair as they walked up to and through the front door. "I'm a little old to be hanging out with a bunch of kindergarteners." She bent down to help Henry get his shoes off.

Henry shook his head. "No you're not. They'll be your friends even if you are old."

She scoffed. "Thanks, kid." They walked to the table and he climbed up and took out his homework folder.

"You don't have many friends to play with," he said as he started pulling out papers.

Emma paused in her movement, thinking about how true her five-year-old's statement was. "I guess not."

"I told my teacher you play with yourself."

Emma's eyes widened almost comically. "You _what_?" She thought back to the attractive brunette woman she had met just a couple of months prior at a parent-teacher conference.

He looked up at her, completely naive to the implication of his words. "I said you were always by yourself and had no other friends to play with and that I wanted you to come with us to the zoo and she said that you could be a shappy roam!" He slid a piece of paper towards her.

"A what?" The blonde took the piece of paper. At the top in bold letters was _Chaperone Form_. So that was the mysterious 'shappy roam.'

"Shappy roams get to come and see the zoo aminals with us!"

She looked at the date filled in. Next Friday. Her day off. Did she really want to spend the day with a bunch of slobbering kids who would probably start complaining and crying by the afternoon?

One look at her son's hopeful face gave her the answer.

* * *

"We have to ride on the bus?" Emma looked up in disbelief at the yellow twinkie that she had avoided since her middle school days. "Well, I guess it's a good thing I got you to be my seat buddy, right?" She smiled down at Henry.

He shook his head. "I'm sitting with Grace."

"Who am I supposed to sit with then?"

Before he could answer, the doors to the bus opened and all the children went running on. The other chaperones lingered behind, ensuring that no one was injured in the mob rushing to get to the seats in the back. Emma noticed that many of the other chaperones were chatting, as if they all knew each other.

 _Probably all on the PTA— or is it PTO?_ Emma thought to herself. This is what she got for not joining parent groups and making friends. She slowly walked up to them, standing near the small brunette she had seen multiple times before and another blonde woman.

"Kathryn! So good to see you! Couldn't get Fred to come along for little Abigail, too?" the brunette asked.

The blonde woman smiled and shook her head. "No, he still had to go to school today. He said he'd try and get a substitute to cover for the next field trip in December."

"There's already another field trip planned for December?" Emma piped in.

The group turned to her. "Of course," the small brunette said. "We have to ensure that there is proper funding, and that we have reserved buses for transportation, and plenty of spaces are open for all of our children to go—"

"Not all parents have as much free time as you, Miss Blanchard," a voice from behind Emma said. "Some have jobs besides campaigning for Mother of the Year."

Emma turned and saw the familiar face of Henry's teacher— Miss Mills. The last few times she had seen her, she always wearing fashionable blouses and skirts or dress pants. Now, however, she wore jeans and a light jacket with a scarf. She had replaced her heels with a sensible pair of boots. A simple outfit, but it looked nothing less than fabulous on her. Emma accidentally let her eyes wander.

The smaller brunette— Miss Blanchard— looked almost mortified. "Regina—"

"Save it, Miss Blanchard," Regina interrupted. She turned and raised an eyebrow at Emma, giving a small nod. "Miss Swan." She turned back to the rest of the parents. "Let's get going, shall we?" Regina tilted her head towards the bus. "After all, we still have a 35 minute drive to the zoo, and in my experience children are not too fond of waiting."

The other chaperones boarded the bus. Emma followed at a slower pace, hoping to not step on Miss Blanchard's toes anymore than she already had. She realized her mistake in doing so when she got to the top of the steps and saw every seat on the bus filled up.

All but one.

With a deep breath and a small smile, Emma sat down on the edge of the seat in the front— right next to Regina Mills.

The bus roared to life and soon they were off.

The ride to the zoo was silent between the two, with only the sounds of yelling children and bickering parents in the background. Once they arrived, the groups were quickly split up and Emma spent the next five hours herding eight kindergarteners around the various exhibits.

By 2:15, the bus had been boarded and they were back on the road. And promptly back to the almost awkward silence between Emma and her son's teacher.

For the first twenty minutes, Emma sat staring out the front window, trying to ignore her surroundings. More children yelling (did they not get tired? what happened to nap time?). More adults bickering (who really cares whether you use canola or vegetable oil? aren't they all the same in the end?). And more silence between her and the woman next to her.

Finally, she had had enough.

"So… Henry mentioned that you guys learned a song about spaghetti Tuesdays the other day?" Smooth, Emma. Smooth.

Miss Mills—Regina— arched an eyebrow. "I assume you are referring to the song 'Today is Monday'?"

"Uh… something about soup?" Emma guessed.

"Indeed. It is a song geared towards teaching children the order of the days of the week in an entertaining and rememberable way," Regina said. She was about to say something else but instead simply closed her mouth and continued looking ahead.

Emma didn't see that as a good sign. "Is… Henry not grasping the concept?"

"No," the brunette said quickly, glancing over at Emma. "He is a smart boy. I was actually looking towards engaging him… further in his pursuit of knowledge."

"Like a gifted students program?" Emma asked, feeling a surge of pride for her son. "I wasn't aware that Storybrooke Elementary had one of those."

"We don't," she said. "I was… considering teaching him one on one, during our break at 1:30, where the children are allowed to choose what activity they want to do for 45 minutes."

Emma furrowed her eyebrows. "What did you want to teach him?"

Regina paused. "Like you said, he has a fondness for the 'Today is Monday' song. I learned it myself growing up, but when my father taught it to me he taught it in his native language. I was considering teaching Henry a few words in Spanish." The corner of her mouth twitched upwards. "He has told me himself he wants to learn to speak every language in the world by the time he is ten."

"He said that?" Emma asked, feeling a pit forming in her stomach. "He's never mentioned it."

The brunette shifted her gaze to the blonde. "I wouldn't take it too personally, Miss Swan. He just mentioned it yesterday, and you know how kids change their minds quite rapidly." Regina cleared her throat. "He did let slip that he believed if he learned all of the languages, he could introduce you to more people so you'd have more friends." She tilted her head as though deep in thought. "I believe he said something about you playing with _yourself?"_

The blonde groaned and rubbed her hands over her face. "Oh, God, I forgot he mentioned to me last week that he told you that." She dropped her hands back to her lap. "It's not what it sounds like—"

"Feeling a little lonely, Miss Swan?" Regina asked, her voice dropping as she looked Emma directly in the eye, an eyebrow quirked upwards once more.

Emma stumbled over her words. "Uh… it's not… he's a kid, he doesn't… I have friends!"

The bus shuddered to a halt and Emma realized they'd already made it back to the school. She took the moment as an escape opportunity and leapt out of her seat, rushing out of the bus to help file kids back into the classroom.

Fifteen minutes later, everyone was all set and Emma and Henry headed towards the VW bug.

"So, kid, did you have fun today?"

Henry was bouncing along beside her. "Lots and lots of fun!" He threw his hands up in the air to punctuate his statement.

Emma noticed his little fist was clenched around something. "Hey, kid, what's in your hand?"

"Oh!" He seemed to startled himself as he unclenched his hand and handed the paper to her. "That's from Miss Mills. I think it's a thank you note for helping out today, because Abigail's mom got one and so did Grace's dad and even Leo's cranky mom got one."

"Hey, be nice," she admonished as she opened up the note. As Henry had predicted, it was a brief, to the point and typed note thanking her for sacrificing her time as a chaperone to help keep the kids happy, yadda, yadda, yadda. What got Emma's attention was the handwritten portion at the end. Her eyes widened as she read it, causing her to glance back towards the bus, where she met Regina's eyes. The teacher gave her a small smirk before turning and walking back into the school. Emma looked back down at the note and re-read Regina's personal note to her.

The first thing listed was a phone number, and underneath in elegant scrawl:

 _For if you ever get tired of playing with just yourself and want to set up a playdate._

 _-Regina_


End file.
